3-Aminopentanenitrile is an important chemical intermediate. For example, it can be used to make 1,3-diaminopentane, which has a variety of uses including its use as an epoxy curing agent, a metal chelating agent, a chain extender for polyurethane formulations, or a monomer for forming polymers including polyamides or polyimides Other uses of 3-aminopentanenitrile include use as an intermediate in the synthesis of pharmaceuticals, as a precursor to amino-acids and amino-amides, and as an intermediate in the formation of specialty reagent chemicals
U.S. Pat. Nos. 4,211,725 and 4,260,556 disclose the reaction of 2-pentenenitrile and “nucleophilic agents,” such as ammonia and ethylenediamine, to produce alkylaminonitriles and dimers Such reactions take place in the presence of a metal addition catalyst
U.S. Pat. No. 4,496,474 discloses the reaction of 2-pentenenitrile and alkylamines to produce the corresponding nitrile compounds
U.S. Pat. No. 5,070,202 discloses the reaction of 2-pentenenitrile and an alkylamine in the presence of 15% to 60% by weight water to produce an alkylaminonitrile
U.S. Pat. No. 5,902,883 discloses the cyanobutylation of ammonia, an alkylamine, or hydrazine with 3-pentenenitrile and 4-pentenenitrile and mixtures thereof to form alkylaminonitriles 3-aminopentanenitrile can, therefore, be prepared by a process of reaction of 2-pentenenitrile with ammonia, aqueous ammonia, or ammonium hydroxide The preferred raw material for this process is a purified 2-pentenenitrile, and not a crude 2-pentenenitrile (e g, a mixture containing 2-pentenenitrile, 2-methyl-2-butenenitrile, and 2-methyl-3-butenenitrile) In this regard, it was believed that significant side reactions would lead to undesirable products and reduced yield of 3-aminopentanenitrile
However, it would be advantageous to use crude 2-pentenenitrile because it eliminates the need for expensive refining of the crude 2-pentenenitrile by, for example, fractional distillation under vacuum, thereby providing an overall more economical process for the manufacture of 3-aminopentanenitrile The present invention provides such a process that can use a crude 2-pentenenitrile to make 3-aminopentanenitrile